Nitrogen containing isethionic acid salts in field ready spray and tank mixes

ABSTRACT

Embodiments of the present invention disclose an agricultural composition that is a field ready spray or a tank mix that includes at least one nitrogen containing isethionic acid salt, at least one agriculturally active ingredient, and at least one surfactant.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to U.S. Provisional Application No.61/172,398, filed Apr. 24, 2009, which is hereby incorporated byreference.

STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT

Not applicable.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates generally to agricultural compositions, inparticular to field ready spray and tank mixes that include nitrogencontaining isethionic acid salts.

BACKGROUND OF THE INVENTION

It is known that multivalent water hardness ions (calcium, magnesium,iron, etc.) can inhibit the efficacy of numerous pesticides, especiallyweak acid herbicides. For example, the efficacy of glyphosate(N-phosphonomethyl glycine) is compromised when combined in a hard watersolution containing calcium and magnesium ions. Calcium and magnesiumions will bind to glyphosate and render it less effective. Thisphenomenon is typical with aminophosphate herbicides as well as otherweak acid herbicides. To overcome this problem, current commercialmanufacturers of weak acid herbicide formulations recommend on theirlabel the inclusion of ammonium sulfate in the spray solution. Numerousresearch studies have shown that ammonium sulfate in the spray tanksolution will reduce the effect of the hard water ions on the efficacyof glyphosate formulations.

However, spray solutions that use ammonium sulfate have drawbacks.Ammonium sulfate grades range in color and purity. Often the applicatoris force to handle large amounts of bulky un-dissolved solid lumps ofammonium sulfate which have absorbed moisture. These materials are hardto handle and do not dissolve easily in the spray solution. This leadsto blocked filter screens in the spray rig and plugged nozzle tipsduring applications.

One way to overcome this disadvantage is to formulate the ammoniumsulfate into a blended tank mix adjuvant formulation. Theseunfortunately can also have limitations and their own unique issues.Current commercial adjuvant formulations that contain ammonium sulfatehave limitations based on the solubility of the ammonium sulfate. Thehigh solids content necessary to achieve the water conditioning effectsfrom the ammonium sulfate may cause incompatibilities in the formulatedtank mix adjuvant. Other components in the formulation may haveincompatibilities due to the lack of water in the product. Similarlythese materials may not be present at proper rates and reduce theoverall efficacy of the ammonium sulfate and the adjuvant component.This may have the further disadvantage of preventing the use of somecompanion herbicides and adjuvants in the spray tank.

The use of ammonium sulfate may limit the efficacy of the pesticide onthe vegetation. The ammonium sulfate formulation may reduce the surfaceproperties of the spray solution in the spray tank and may limit theeffectiveness of the pesticide on the target organism.

BRIEF SUMMARY OF SOME OF THE PREFERRED EMBODIMENTS

In a first aspect, embodiments of the present invention disclose anagricultural composition that is a field ready spray or a tank mix thatincludes at least one nitrogen containing isethionic acid salt, anagriculturally active ingredient, and at least one surfactant.

In an embodiment of the present invention, the at least one nitrogencontaining isethionic acid salt has a cationic nitrogen containing groupthat is an alkyl amine, an alkylalkanolamine or a cyclic amine.

In an embodiment of the present invention, the at least one nitrogencontaining isethionic acid salt comprises ammonium isethionic acid salt.

In an embodiment of the present invention, the at least one nitrogencontaining isethionic acid salt comprises tallow amine isethionic acidsalt.

In an embodiment of the present invention, the at least one nitrogencontaining isethionic acid salt comprises a derivative of a nitrogencontaining isethionic acid salt.

In an embodiment of the present invention, the derivative of thenitrogen containing isethionic acid salt comprises nitrogen containingisethionic methyl acid salt.

In an embodiment of the present invention, the at least one nitrogencontaining isethionic acid salt further comprises isethionic acid.

In an embodiment of the present invention, the agriculturally activeingredient is a weak acid agriculturally active ingredient.

In an embodiment of the present invention, the agriculturally activeingredient is n-phosphonomethylglycine (glyphosate) present in any ofits commonly used agriculturally acceptable salts.

In an embodiment of the present invention, the agriculturally activeingredient is selected from the group consisting of: an insecticide, afungicide, a biocide, a molluscicide, an algaicide, a plant growthregulator, an anthelmintic, a rodenticide, a nematocide, an acaricide,an amoebicide, a protozoacide, a crop safener and a combination thereof.

In an embodiment of the present invention, the at least one surfactantcomprises one or more surface active agents capable of reducing thesurface tension of water.

In a second aspect of the present invention, a method of treatment ofvegetation is disclosed comprising the step of contacting theagricultural composition to vegetation. The agricultural composition isa field ready spray or a tank mix that includes at least one nitrogencontaining isethionic acid salt, an agriculturally active ingredient,and at least one surfactant.

In a third aspect, embodiments of the present invention disclose amethod of treatment of a substrate comprising the step of contacting theregisterable, stable agricultural formulation to the stable registerableformulation to the substrate requiring treatment.

In a fourth aspect, embodiments of the present invention disclose anagricultural adjuvant composition that includes at least one nitrogencontaining isethionic acid salt and at least one surfactant.

The foregoing has outlined rather broadly the features of the presentinvention in order that the detailed description of the invention thatfollows may be better understood. Additional features and advantages ofthe invention will be described hereinafter that form the subject of theclaims of the invention. It should be appreciated by those skilled inthe art that the conception and the specific embodiments disclosed maybe readily utilized as a basis for modifying or designing othercompositions for carrying out the same purposes of the presentinvention. It should also be realized by those skilled in the art thatsuch equivalent compositions do not depart from the spirit and scope ofthe invention as set forth in the appended claims.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

In embodiments of the present invention, it has now been surprisinglyfound that of field ready sprays and tank mixes containing weak acidherbicides and nitrogen containing isethionic acid salts typically haveunique water conditioning characteristics and enhanced biologicalefficacy.

Embodiments of the present invention disclose an agriculturalcomposition that includes at least one nitrogen containing isethionicacid salt, an agriculturally active ingredient, and at least onesurfactant. The agricultural composition is a field ready spray or atank mix.

Embodiments of the present invention include at least one nitrogencontaining isethionic acid salt. The nitrogen containing species of thesalt may be any cationic nitrogen containing group. Examples of cationicnitrogen containing groups may be alkyl amines, alkoxylated alkylaminesand cyclic amines. Specific examples of the nitrogen containing groupmay include ammonium, alkyl amines and their ethoxylated derivatives,fatty amines (e.g. tallow amine, coco amine and soya amines) and theirethoxylated derivatives, ethyleneamines, ethanolamines, morpholines,substituted propylamines, polyol amines (such as JEFFAMINE® amines asavailable from Huntsman Corporation of The Woodlands, Texas),N-alkylalkyldiamines and their alkoxylated derivatives,N,N-alkyldiamines and their alkoxylated derivatives and combinationsthereof. One skilled in the art will recognize appropriate nitrogencontaining cationic species to use in embodiments of the presentinvention.

The anionic part of the salt includes isethionic acid. Isethionic acidhas the general formula HSO₃—CH₂—CH₂—OH. Two versions of isethionicacid, the second being a derivative of the first (isethionic methylacid), may be produced using the following reactions:

The isethionic acid is neutralized to form the salt. The isethionic acidmay be neutralized, separately or in combination, with such reactants asammonia, and other nitrogen containing groups listed above and/or tallowamine ethoxylates. For example, a tallow amine ethoxylate would form thefollowing salt with isethionic acid.

TALLOW AMINE ETHOXYLATE→R-N⁻(EO)_(X&Y)

H⁺SO₃—CH₂—CH₂—OH

The nitrogen containing isethionic acid salt may further includeisethionic acid (non-nueutralized species). In another embodiment, thenitrogen containing isethionic acid salt comprises a derivatives ofnitrogen containing isethionic acid salts. An example of a derivative ofa nitrogen containing isethionic acid salt would be nitrogen containingisethionic methyl acid salt (whose non-neutralized acid is featuredabove). One skilled in the art, with the benefit of this disclosure,will recognize appropriate nitrogen containing isethionic acid salts foruse in the present invention.

Embodiments of the present invention include at least one agriculturallyactive ingredient. The agriculturally active ingredients may includewater soluble herbicides, fertilizers and combinations thereof,including without limitation, aminophosphate herbicides. In anembodiment, the agriculturally active ingredient is a weak acidherbicide. Weak acid herbicides may include without limitation,glyphosate, glufosinate, bipyridlylquaternary ammonium salts(bipyridinium salt) such as paraquat and diquat, salts of phenoxy acidssuch as 2,4-dichlorophenoxyacetic acid, meta-chlorophenoxyacetic acid(MCPA), picloram, triclopyr and fluroxypyr, and bromoxynil.

As used herein, “glyphosate” means N-phosphonomethylglycine in its acidform or any agriculturally acceptable salt thereof as well as anycomposition or formulation containing a glyphosate herbicide.“Glyphosate herbicide” means any form of glyphosate which in aqueoussolution provides glyphosate anions along with suitable cations orglyphosate acid. Examples of such suitable cations are alkali metalcations, for instance sodium and potassium, and ammonium and substitutedammonium cations. The latter include cations derived from primary orsecondary amines such as isopropylamine or dimethylamine, and fromdiamines such as ethylenediamine. Glyphosate herbicide includes theisopropylamine salts of glyphosate and other agriculturally acceptablesalts of glyphosate such as those disclosed in U.S. Pat. No. 3,799,758.Further, examples of agriculturally acceptable salts of glyphosate aretrimethyl-sulfonium salt (“sulfosate”) or aminoguanidine salts asdisclosed in EP-A-0 088 180. Because glyphosate has more than onereplaceable hydrogen atom, mono- and di-salts are possible, as well asmixtures of such salts. Typical glyphosate salts are the potassium,ammonium and trimethylsulphonium salts as well as the mixedalkylsulfonium salts and trialkylammonium salts.

As used herein, “glufosinate” means N-phosphonomethylalanine in its acidform or any agriculturally acceptable salt of thereof including withoutlimitation the ammonium salt.

In another embodiment of the present invention, the agriculturallyactive ingredient is a fertilizer. Suitable fertilizers may include,without limitation, inorganic and/or organic fertilizers, fertilizingsalts, and mineral fertilizers such as urea, urea phosphate,urea-containing mixed fertilizers, ammonium nitrate, ammoniumsulfate-nitrate, ammonium sulfate, mono- and di-ammonium phosphate,monopotassium phosphate, Chilean nitrate, potassium-ammonium phosphate,potassium chloride, potassium nitrate, potassium phosphate, potassiumsulfate, sodium nitrate, nitrogenous fertilizers, potassium salts, N, P,K-compound fertilizers, N, P, K-compound fertilizers containing traceelements and combinations of such fertilizers and mineral fertilizers.

Suitable fertilizers may also include chlorides, sulfates, or nitratesof Ca, Mg, Fe, Ni, Mn, Zn, Cu, and Co as well as Mo in the form ofwater-soluble molybdates and boron in the form of boric acid or boricanhydride. These fertilizers may be in complexed or partially complexedform in order to ensure water solubility. These fertilizers may becomplexed with alkali metal salts of N-carboxyalkyl-amino acids. Oneskilled in the art will recognize other suitable fertilizers for usewith this invention.

In other embodiments, the agriculturally active ingredient may include,without limitation: insecticides, fungicides, biocides, molluscicides,algaicides, plant growth regulators, anthelmintics, rodenticides,nematocides, acaricides, amoebicides, protozoacides, crop safeners andcombinations thereof. Examples of such agricultural ingredients can bedrawn from the Pesticide Dictionary (contained in the Farm ChemicalsHandbook) or the British Crop Protection Society: Pesticides Manual, thecontents of which are incorporated herein by reference. Agriculturallyactive ingredients further include chemical substances that aredescribed as “biologically-active ingredients” in InternationalPublication No. WO 2010/009820, which is hereby incorporated byreference. WO 2010/009820 includes, without limitation, descriptions andlists of various pesticides, fungicides, herbicides, insecticides, plantgrowth regulators, rodenticides, miticides, moluscicides, nematicidesand antimicrobials which may be used in embodiments of the presentinvention. One skilled in the art, with the benefit of this disclosure,will recognize suitable agriculturally active ingredients andcombinations thereof for use in this invention.

Embodiments of the present invention include at least one surfactant.The at least one surfactant may include one or more surface activeagents capable of reducing the surface tension of water. Surfactants ofthe present invention may include, without limitation, phosphate estersof akyl ethoxylates and/or alkylaryl ethoxylates; alkylamine ethoxylatesand/or etheramine ethoxylates; ethanolamines (such as monoethanolamine(MEA), diethanolamine (DEA), triethanolamine (TEA)) and combinationsthereof. Surfactants generally include all surfactants which may show upin the field spray solution or a tank mix. Such surfactants may include,without limitation: aldypolysaccarides, sorbitol and sorbitan esters andethoxylates of such esters, fatty acid ethoxylates ethoxylated fattyalkanolamines, sulfosuccinates, naphthalene sulfonates, polyoxyethylenepolyoxypropylene co-block polymers, alkyl polyoxyethylenepolyoxypropylene copolymers, alkyl ethoxylates, aklyaryl ethoxylates,alcohol ether sulfates, alcohol sulfates, alpha olefin sulfonates, saltsof dodecylbenzene sulfonic acid, and combinations thereof. One skilledin the art will recognize other suitable surfactants for use inembodiments of the present invention.

Compositions disclosed herein may further comprise other additives.Additives may include but are not limited to utility additivesincluding: humectants, antifoaming agents, dyes and non-surfactantadjuvants such as ammonium sulphate.

Agriculture compositions of the present invention are field ready spraysor tank mixes. Tank mixes are combinations or agricultural products thata consumer, such as a farmer, would pour into a tank, add water andperhaps other adjuvants/additives, mix and then spray/apply on thefield. These mixes are typically not stable for extended periods oftime, though some of them may have this characteristic. Field readysprays or tank mixes are distinguishable from stable commercialformulations that have an appreciable stable shelf life and typicallyneed government (for example, FIFRA) registration numbers. Field readysprays are typically are prepared close to the field to which thematerial is to be applied. In contrast a commercial pesticideformulation would be formulated at a government approved manufacturingsite and in such a concentration that the product must be diluted inwater for application.

Embodiments of the present invention further disclose an agriculturaladjuvant composition comprising at least one nitrogen containingisethionic acid salt and at least one surfactant. These adjuvants can beused in field ready sprays or tank mixes.

Embodiments of the present invention also disclose a method of treatmentof vegetation comprising the step of contacting the agriculturalcompositions of the present invention to vegetation or soil.Compositions of the present invention may be applied to plants andsoils.

Embodiments of the present invention also disclose a method of treatmentof a substrate comprising the step of contacting the agriculturalcompositions of the present invention to the substrate. Such examplesmay include public health uses of pesticides or animal healthformulations. As an example, insecticides may be applied to floors andwalls as a preventative treatment. Also, fungicides may be applied toseeds and soils. Compositions of the present invention may be used inother appropriate applications.

The present invention will be further illustrated by a consideration ofthe following examples, which are intended to be exemplary of theinvention.

Examples

The following adjuvant compositions were produced.

TABLE 1 Material Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. 5 Ex. 6 Ex. 7 Ex. 8 Ex. 9Ex. 10 Ex. 11 Isethionic Acid 100 96.5 96.4 96.3 95.7 95.5 95 90 85 70100% SURFONIC ® SI 100 surfactant intermediate Ammonium 3.5 3.6 3.7Hydroxide Sodium Hydroxide 4.3 4.5 50% SURFONIC ® T-5 5 10 15 30Surfactant

Examples 1-11 Compared With Control Example

Isethionic acid (Example 1) and ten neutralization products ofisethionic acid (Examples 2-11) were used to treat aqueous spray tanksolutions of isopropylamine glyphosate in order to measure the waterconditioning efficacy of isethionic acid and the other isethionates.Isethionic acid was neutralized with sodium (Examples 2, 6, and 7),ammonia (Examples 3-5) and tallow amine ethoxylates (Examples8-11—SURFONIC® T-5 surfactant). These candidates were evaluated againstthe standard agricultural water conditioner, ammonium sulfate in anaqueous tank mix of isopropylamine glyphosate (Control Example).Specifically, the candidates were tested for their ability to conditionwater as a function of the suppression of water hardness inhibition ofpesticides, such as glyphosate. All evaluations were run in the absenceof any surfactant in standard hard water as defined by the World HealthOrganization standard hard waters. The evaluations were run ingreenhouse conditions over a variety of plant species, includingdetermining injury to crop species. The reported data was percentcontrol of target weed species and percent injury to crop species. Allevaluations (except for one industry standard) were conducted in theabsence of any surfactant.

The surprising result in these determinations was that the isethionicacid and its neutralants functioned at a level comparable to that of theagricultural industry standard ammonium sulfate.

Examples 12 and 13 show embodiments of agricultural adjuvantcompositions. Two compositions were produced and are shown in Table 2.The surfactants used are SURFONIC® N-95 surfactant and TERWET® 3001adjuvant. SURFONIC® N-95 surfactant is a nonylphenol ethoxylate. TERWET®3001 is a C₈-₁₀ alkyl polyglucoside. Both surfactants are commerciallyavailable from Huntsman Corporation of The Woodlands, Texas.

TABLE 2 Ingredients Example 12 Example 13 SURFACTANT SURFONIC ® N-95SURFACTANT 60.0 TERWET ® 3001 ADJUVANT 15.0 NH₄ISETHIONATE 20.0 58.0WATER (DEIONIZED) 20.0 2.0 GLYCERINE 25.0 100.0 100.0 Results: CLEARCLEAR

Examples 12 and 13 show that clear, homogeneous formulations can be madewith ammonium isethionate.

Although the present invention and its advantages have been described indetail, it should be understood that various changes, substitutions andalterations may be made herein without departing from the spirit andscope of the invention as defined by the appended claims.

What is claimed is:
 1. An agricultural composition comprising: a) atleast one nitrogen containing isethionic acid salt, b) at least oneagriculturally active ingredient, c) at least one surfactant, andwherein the agricultural composition is a field ready spray or a tankmix.
 2. A composition according to claim 1 wherein the at least onenitrogen containing isethionic acid salt has a cationic nitrogencontaining group that is an alkyl amine, an alkylalkanolamine or acyclic amine.
 3. A composition according to claim 1 wherein the at leastone nitrogen containing isethionic acid salt comprises ammoniumisethionic acid salt.
 4. A composition according to claim 1 wherein theat least one nitrogen containing isethionic acid salt comprises tallowamine isethionic acid salt.
 5. A composition according to claim 1wherein the at least one nitrogen containing isethionic acid saltcomprises a derivative of a nitrogen containing isethionic acid salt. 6.A composition according to claim 5 wherein the derivative of a nitrogencontaining isethionic acid salt comprises nitrogen containing isethionicmethyl acid salt.
 7. A composition according to claim 1 wherein the atleast one nitrogen containing isethionic acid salt further comprisesisethionic acid.
 8. A composition according to claim 1 wherein theagriculturally active ingredient comprises a weak acid agriculturallyactive ingredient.
 9. A composition according to claim 1 wherein theagriculturally active ingredient comprises n-phosphonomethylglycine. 10.A composition according to claim 1 wherein the agriculturally activeingredient is selected from the group consisting of: an insecticide, afungicide, a biocide, a molluscicide, an algaicide, a plant growthregulator, an anthelmintic, a rodenticide, a nematocide, an acaricide,an amoebicide, a protozoacide, a crop safener and a combination thereof.11. A composition according to claim 1 wherein the at least onesurfactant comprises one or more surface active agents capable ofreducing the surface tension of water.
 12. A method of treatment ofvegetation comprising the step of contacting the agriculturalcomposition as described in claim 1 to vegetation or soil.
 13. A methodof treatment of a substrate comprising the step of contacting theagricultural composition as described in claim 1 to the substrate. 14.An agricultural adjuvant composition comprising: a) at least onenitrogen containing isethionic acid salt, and b) at least onesurfactant.